Patents Assigned to Nihon Tokushu Noyaku Seizo K.K.
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Patent number: 5001138Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.Type: GrantFiled: May 4, 1989Date of Patent: March 19, 1991Assignee: Nihon Tokushu Noyaku Seizo, K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
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Patent number: 4988712Abstract: Novel insecticidally active heterocyclic compounds of the formula ##STR1## wherein W represents a substituted pyridyl group, or a 5- or 6-membered optionally substituted heterocyclic group containing at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms,R represents a hydrogen atom or an alkyl group,Y represents =N-- or ##STR2## R' represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group or a cyano group,Z represents a nitro group or a cyano group, andT represents 3 or 4 optionally substituted ring members of a 5- or 6-membered unsaturated heterocyclic ring which it forms together with the adjoining carbon atom and nitrogen atom, said 5- or 6-membered unsaturated heterocyclic ring containing 1 to 3 hetero atoms which are selected from oxygen, sulfur and nitrogen atoms and at least one of which is a nitrogen atom.Type: GrantFiled: August 14, 1989Date of Patent: January 29, 1991Assignee: Nihon Tokushu Noyaku Seizo, K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
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Patent number: 4971619Abstract: Herbicidal benzothiazolones of the formula ##STR1## wherein X represents hydrogen or halogen, R.sup.1 represents hydrogen, alkyl, various organic radicals, ##STR2## in which R.sub.2, R.sup.4, R.sup.5 and R.sup.6 each is hydrogen or an organic radical, and R.sup.3 is alkyl, cycloalkyl or optionally halo-substituted phenyl.Type: GrantFiled: July 12, 1989Date of Patent: November 20, 1990Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Shigeki Yagi, Hiroshi Miyauchi
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Patent number: 4960780Abstract: Nitro-substituted heterocyclic compounds of the formula (I) ##STR1## wherein R is hydrogen or alkyl,Z is an optionally substituted aryl or optionally substituted heterocyclic groun containing at least one atom selected from N, O and S,A is optionally substituted ethylene or optionally substituted trimethylene, andB stands for 2 or 3 members of a heterocyclic ring which is formed, together with the adjacent C-atom and N-atom and at least one of said members may represent a hetero atom and may be optionally substituted, provided that when B stands for 3 members, two of which are carbon atoms and the other one is a nitrogen atom which is located in the middle of the three members, then at least one of said two carbon atoms must be substituted by a keto group. Such compounds being useful as insecticides.Type: GrantFiled: May 17, 1989Date of Patent: October 2, 1990Assignee: Nihon Tokushu Noyaku Seizo K. K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
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Patent number: 4940483Abstract: Fungicidal and herbicidal novel 3-substituted pyridines of the formula ##STR1## wherein A represents oxygen or sulfur,B represents oxygen, sulfur or sulfinyl,R.sup.1 represents hydrogen, halogen, alkyl or haloalkyl,R.sup.2 represents hydrogen, halogen, alkyl, phenyl, haloalkyl or phenoxy,l is 0 or 1,m is an integer from 1 to 4,n is an integer from 1 to 5, andW represents ##STR2## in which R.sup.3 and R.sup.4 each represent hydrogen, hydroxyalkyl, alkoxyalkyl, alkyl, benzyloxyalkyl, haloalkyl or carboxyalkyl, orR.sup.3 and R.sup.4 form a hydrocarbon ring having 3 to 12 carbon atoms in total together with the carbon atoms to which they are bonded, andR.sup.5, R.sup.6, R.sup.7 and R.sup.8 each represents hydrogen, alkyl or hydroxyalkyl, provided that none of R.sup.1, R.sup.2, R.sup.3, and R.sup.Type: GrantFiled: November 8, 1988Date of Patent: July 10, 1990Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Yoshio Kurahashi, Toshio Goto, Kunihiro Isono, Yoshinori Kitagawa, Tetsuji Izumi, Toshihito Kondo, Takayo Sato
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Patent number: 4914113Abstract: The present invention relates to novel imidazolines of the formula (I) ##STR1## to processes for their production and to their use as very potent insecticides.In formula (I) aboveR represents hydrogen or alkyl,Y represents nitro or cyano,W represents an optinally substituted 5- or 6-membered group having at least one hetero-atom selected from the group consisting of nitrogen, oxygen and sulfur atoms, andZ represents alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, haloalkenyl, aralkyl, acyl or --CH.sub.2 --W (wherein W has the meaning stated above).Type: GrantFiled: November 1, 1988Date of Patent: April 3, 1990Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
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Patent number: 4909828Abstract: Herbicidal 2,5-dihydropyrroles of the formula ##STR1## wherein A represents hydroxy, halogen, an alkylcarbonyloxy group having alkyl with 1 to 4 carbon atoms optionally substituted by halogen, or an alkylsulfonyloxy group having 1 to 4 carbon atoms optionally substituted by halogen,X represents CH or N, andR.sup.1, R.sup.2 and R.sup.3 each represent hydrogen, or an alkyl group having 1 to 4 carbon atoms optionally substituted by halogen, with the proviso that all of R.sup.1, R.sup.2 and R.sup.3 do not simultaneously represent hydrogen,or R.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, may form an alicyclic ring with 3 to 6 carbon atoms.Intermediates of the formula ##STR2## are also new.Type: GrantFiled: April 13, 1989Date of Patent: March 20, 1990Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Hiroshi Miyauchi
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Patent number: 4902335Abstract: Herbicidal benzo-fused cyclic compounds of the formula ##STR1## wherein Q is ##STR2## Y is O or S, W is ##STR3## T is O, S, --NH-- or ##STR4## and R.sup.4 may represent, together with T, chlorine,Z is O or S,X is hydrogen or halogen,n is 0 or 1 andR is C.sub.3-6 cycloalkyl, an optionally substituted 5-membered heterocyclic group or an optionally substituted 6-membered heteroaromatic group which contains one to three nitrogen atoms,and salts thereof.Type: GrantFiled: June 17, 1988Date of Patent: February 20, 1990Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Shigeki Yagi, Hiroshi Miyauchi, Katsuhiko Shibuya
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Patent number: 4882344Abstract: Novel insecticidally active heterocyclic compounds of the formula ##STR1## wherein W represents a substituted pyridyl group, or a 5- or 6-membered optionally substituted heterocyclic group containing at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms,R represents a hydrogen atom or an alkyl group,Y represents .dbd.N-- or ##STR2## R' represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group or a cyano group,Z represents a nitro group or a cyano group, andT represents 3 or 4 optionally substituted ring members of a 5- or 6-membered unsaturated heterocyclic ring which it forms together with the adjoining carbon atom and nitrogen atom, said 5- or 6-membered unsaturated heterocyclic ring containing 1 to 3 hetero atoms which are selected from oxygen, sulfur and nitrogen atoms and at least one of which is a nitrogen atom.Type: GrantFiled: September 13, 1988Date of Patent: November 21, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
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Patent number: 4880933Abstract: Novel intermediates for insecticides of the formula (I) ##STR1## wherein Y represents nitro or cyano;A represents an ethylene or trimethylene radical, which is optionally substituted; andZ can have many possible meanings.Type: GrantFiled: December 8, 1987Date of Patent: November 14, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Koichi Moriya, Katsuhiko Shibuya
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Patent number: 4876263Abstract: Nitro-subsliluted heterocyclic compounds of the formula (I) ##STR1## wherein R is hydrogen or alkyl, Z is an optionally substituted aryl or optionally subtituted heterocyclic groun containing at least one atom selected from N, O and S,A is optionally substituted ethylene or optionally substituted trimethylene, andB stands for 2 or 3 members of a heterocyclic ring which is formed, together with the adjacent C-atom and N-aom and at least one of said members may represent a hetero atom and may be optionally substituted, provided that when B stands for 3 members, two of which are carbon atoms and the other one is a nitrogen atom which is located in the middle of the three members, then at least one of said two carbon atoms must be substituted by a keto group. Such compounds being useful as insecticides.Type: GrantFiled: June 17, 1988Date of Patent: October 24, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
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Patent number: 4857556Abstract: Substituted benzylcycloalkenylurea derivatives of the formula (I) ##STR1## wherein X represents a halogen atom or a lower alkyl group, Y represents an oxygen atom or a sulfur atom,R.sup.1 represents a cycloalkenyl group andR.sup.2 represents a lower alkyl group, a cycloalkyl group, a benzyl group or a phenyl group optionally substituted by 1 to 5 substituents selected from the group consisting of a hydroxyl group or a lower alkoxy groupand their use as fungicides. They can be synthesized, for example, by reacting of a substituted benzyl-cycloalkenylamine with an isocyanate or by reacting of a carbamoyl halide with an amine. The starting material, the substituted benzyl-cycloalkenyl amines, are also new.Type: GrantFiled: December 8, 1987Date of Patent: August 15, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Yasuo Yamada, Junichi Saito, Tatsuo Tamura, Shinji Sakawa
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Patent number: 4849432Abstract: Novel heterocyclic compounds of the formula ##STR1## wherein, R.sup.1 represents a hydrogen atom or an alkyl group, A represents an ethylene group which may be substituted by alkyl or a trimethylene group which may be substituted by alkyl, X represents an oxygen or sulfur atom or the group ##STR2## in which R.sup.2 represents a hydrogen atom of an optionally substituted alkyl, an alkenyl, an alkynyl or an acyl group, and R.sup.3 represents a hydrogen atom or an alkyl group, and Z represents an optionally sibstituted 5- or 6-membered heterocyclic group which contains at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms, or an optionally substituted 3- or 4-pyridyl group.The above defined novel heterocyclic compounds of formula (I) exhibit powerful insecticidal properties.Type: GrantFiled: February 24, 1987Date of Patent: July 18, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori
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Patent number: 4845230Abstract: Herbicidally active novel 2,5-dihydropyrroles of the formula ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.2 and R.sup.3 each represent an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms or together may form a C.sub.2 -C.sub.6 alkylene group which may be substituted by halogen, and R represents a hydroxy group, a mercapto group, a halogen atom, an amino group or a group of the formula --O--W in which W represents an alkylcarbonyl, a halogenoalkylcarbonyl, an alkoxycarbonyl or a halogenoalkoxycarbonyl group each having 1 to 4 carbon atoms in the alkyl group, an alkylsulfonyl or a halogenoalkylsulfonyl group each having 1 to 4 carbon atoms in the alkyl group or a di-C.sub.1 -C.sub.4 -alkylamino sulfonyl group.Type: GrantFiled: November 22, 1988Date of Patent: July 4, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Shigeki Yagi, Hiroshi Miyauchi
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Patent number: 4845106Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.Type: GrantFiled: July 1, 1987Date of Patent: July 4, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
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Patent number: 4836844Abstract: Novel herbicidally active N-benzothiazolyl-2-5-dihydropyrroles of the formula ##STR1## in which R is hydrogen or an acyl group,X is a halogen atom, an alkyl group, a haloalkyl group, a haloalkoxy group or a phenyl group,n is 0, 1 or 2, andY is an alkyl group.Type: GrantFiled: June 25, 1987Date of Patent: June 6, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Hidenori Hayakawa, Shigeki Yagi
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Patent number: 4828604Abstract: Herbicidally active novel 2,5-dihydropyrroles of the formula ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.2 and R.sup.3 each represent an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms or together may form a C.sub.2 -C.sub.6 alkylene group which may be substituted by halogen, and R represents a hydroxy group, a mercapto group, a halogen atom, an amino group or a group of the formula --O--W in which W represents an alkylcarbonyl, a halogenoalkylcarbonyl, an alkoxycarbonyl or a halogenoalkoxycarbonyl group each having 1 to 4 carbon atoms in the alkyl group, an alkylsulfonyl or a halogenoalkylsulfonyl group each having 1 to 4 carbon atoms in the alkyl group or a di-C.sub.1 -C.sub.4 -alkylamino sulfonyl group.Type: GrantFiled: March 9, 1988Date of Patent: May 9, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Shigeki Yagi, Hiroshi Miyauchi
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Patent number: 4812571Abstract: Intermediates, for insecticides, of the formula ##STR1## in which R is a hydrogen atom or a lower alkyl group,X is a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a lower alkenyl group or a lower alkynyl group; a phenyl, phenoxy, phenylthio, naphthyl, naphthoxy or naphthylthio group which may optionally be substituted by halogen; or a benzyl, phenethyl or naphthylmethyl, group,l is 1, 2, 3 or 4,m is 2, 3 or 4, andn is 0, 1, 2 or 3.Type: GrantFiled: December 9, 1987Date of Patent: March 14, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
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Patent number: 4812454Abstract: The present invention provides novel nitromethylene derivatives of the formula (I) ##STR1## wherein R represents a hydrogen atom or an alkyl group, X represents a haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, nitro, cyano, thiocyanato, haloalkenyl, haloalkynyl, hydroxyl, alkoxycarbonyl, amino, acyl, dialkylamino, aclamino or alkoxy group, l represents 1, 2 or 3 provided that when l is 1, X does not represent an alkoxy group and when l is 2 or 3, not all substituents X represent an alkoxy group, m represent 2, 3 or 4, and n represents 0 or 1, and the use of the new compounds as insecticides.Type: GrantFiled: October 19, 1987Date of Patent: March 14, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya, Bernd Baasner
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Patent number: 4806553Abstract: There are provided insecticidally active alkylenediamines of the formula ##STR1## wherein W.sup.1 stands for a 5- or 6-membered heterocyclic group which may be substituted, containing at least one hetero atom selected from, O, S and N, R.sup.1, R.sup.2 and R.sup.3 are hydrogen or alkyl and R.sup.4, X, Y and Z have the meanings as given in the specification.The new alkylenediamines can be prepared according to different preparation methods and exhibit a strong insecticidal activity.Type: GrantFiled: June 18, 1987Date of Patent: February 21, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori